Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C3H5NO2 |
| Molecular Weight | 87.0773 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(=O)C1CO1
InChI
InChIKey=FMAZQSYXRGRESX-UHFFFAOYSA-N
InChI=1S/C3H5NO2/c4-3(5)2-1-6-2/h2H,1H2,(H2,4,5)
| Molecular Formula | C3H5NO2 |
| Molecular Weight | 87.0773 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| N-Acetyl-S-(1-carbamoyl-2-hydroxy-ethyl)-L-cysteine (iso-GAMA) a further product of human metabolism of acrylamide: comparison with the simultaneously excreted other mercaptuic acids. | 2009-07 |
|
| DNA adduct formation and induction of micronuclei and mutations in B6C3F1/Tk mice treated neonatally with acrylamide or glycidamide. | 2009-05-01 |
|
| Validation of a food frequency questionnaire measurement of dietary acrylamide intake using hemoglobin adducts of acrylamide and glycidamide. | 2009-04 |
|
| Toxicokinetics of acrylamide in rats and humans following single oral administration of low doses. | 2009-03-01 |
|
| Acrylamide in children--exposure assessment via urinary acrylamide metabolites as biomarkers. | 2009-03 |
|
| Investigation of the low-dose response in the in vivo induction of micronuclei and adducts by acrylamide. | 2009-01 |
|
| Simultaneous determination of acrylamide, its metabolite glycidamide and antipyrine in human placental perfusion fluid and placental tissue by liquid chromatography-electrospray tandem mass spectrometry. | 2008-12-15 |
|
| Evidence-based dose-response assessment for thyroid tumorigenesis from acrylamide. | 2008-12 |
|
| Rapid and sensitive HILIC-ESI-MS/MS quantitation of polar metabolites of acrylamide in human urine using column switching with an online trap column. | 2008-11-12 |
|
| Transplacental transfer of acrylamide and glycidamide are comparable to that of antipyrine in perfused human placenta. | 2008-11-10 |
|
| Low-acrylamide French fries and potato chips. | 2008-10 |
|
| Human CYP2E1 mediates the formation of glycidamide from acrylamide. | 2008-10 |
|
| Carcinogenicity of acrylamide: a computational study. | 2008-09-24 |
|
| Genotoxicity of glycidamide in comparison to 3-N-nitroso-oxazolidin-2-one. | 2008-08-13 |
|
| Cross-sectional study on acrylamide hemoglobin adducts in subpopulations from the European Prospective Investigation into Cancer and Nutrition (EPIC) Study. | 2008-08-13 |
|
| Approach for cancer risk estimation of acrylamide in food on the basis of animal cancer tests and in vivo dosimetry. | 2008-08-13 |
|
| Acrylamide carcinogenicity. | 2008-08-13 |
|
| Hemoglobin adducts and mercapturic acid excretion of acrylamide and glycidamide in one study population. | 2008-08-13 |
|
| Development of a stable isotope dilution assay for the quantitation of glycidamide and its application to foods and model systems. | 2008-08-13 |
|
| Biomonitoring Equivalents (BE) dossier for acrylamide (AA) (CAS No. 79-06-1). | 2008-08 |
|
| Internal doses of acrylamide and glycidamide in mice fed diets with low acrylamide contents. | 2008-08 |
|
| The effects of subchronic acrylamide exposure on gene expression, neurochemistry, hormones, and histopathology in the hypothalamus-pituitary-thyroid axis of male Fischer 344 rats. | 2008-07-15 |
|
| Acrylamide exposure and incidence of breast cancer among postmenopausal women in the Danish Diet, Cancer and Health Study. | 2008-05-01 |
|
| Minireview on the toxicity of dietary acrylamide. | 2008-04 |
|
| Genotoxic effects of acrylamide and glycidamide in mouse lymphoma cells. | 2008-02 |
|
| Effects of perinatal exposure to acrylamide and glycidamide on intestinal tumorigenesis in Min/+ mice and their wild-type litter mates. | 2008-01-30 |
|
| Approaches to acrylamide physiologically based toxicokinetic modeling for exploring child-adult dosimetry differences. | 2007-12 |
|
| Urinary metabolites as biomarkers of acrylamide exposure in mice following dietary crisp bread administration or subcutaneous injection. | 2007-12 |
|
| Assessment of the relation between biomarkers for smoking and biomarkers for acrylamide exposure in humans. | 2007-11 |
|
| Expression profile of human cells in culture exposed to glycidamide, a reactive metabolite of the heat-induced food carcinogen acrylamide. | 2007-10-30 |
|
| Analysis of hemoglobin adducts of acrylamide and glycidamide by liquid chromatography-electrospray ionization tandem mass spectrometry, as exposure biomarkers in French population. | 2007-10-12 |
|
| Acrylamide effects on kinesin-related proteins of the mitotic/meiotic spindle. | 2007-07-01 |
|
| Comparison of estimated dietary intake of acrylamide with hemoglobin adducts of acrylamide and glycidamide. | 2007-07 |
|
| An absorption study of dietary administered acrylamide in swine. | 2007-07 |
|
| Urinary acrylamide metabolites as biomarkers for short-term dietary exposure to acrylamide. | 2007-06 |
|
| Physiologically based pharmacokinetic/pharmacodynamic model for acrylamide and its metabolites in mice, rats, and humans. | 2007-03 |
|
| Urinary excretion of acrylamide and metabolites in Fischer 344 rats and B6C3F(1) mice administered a single dose of acrylamide. | 2007-02-28 |
|
| Cytogenetic damage induced by acrylamide and glycidamide in mammalian cells: correlation with specific glycidamide-DNA adducts. | 2007-02 |
|
| Reaction of glycidamide with 2'-deoxyadenosine and 2'-deoxyguanosine--mechanism for the amide hydrolysis. | 2007 |
|
| Acrylamide exposure via the diet: influence of fasting on urinary mercapturic acid metabolite excretion in humans. | 2006-12 |
|
| Metabolism of acrylamide to glycidamide and their cytotoxicity in isolated rat hepatocytes: protective effects of GSH precursors. | 2006-12 |
|
| Relationships between biomarkers of exposure and toxicokinetics in Fischer 344 rats and B6C3F1 mice administered single doses of acrylamide and glycidamide and multiple doses of acrylamide. | 2006-11-15 |
|
| Quantitation of mercapturic acids from acrylamide and glycidamide in human urine using a column switching tool with two trap columns and electrospray tandem mass spectrometry. | 2006-10-27 |
|
| Acrylamide, an in vivo thyroid carcinogenic agent, induces DNA damage in rat thyroid cell lines and primary cultures. | 2006-09-26 |
|
| Acrylamide: review of toxicity data and dose-response analyses for cancer and noncancer effects. | 2006-09-16 |
|
| Urinary mercapturic acids and a hemoglobin adduct for the dosimetry of acrylamide exposure in smokers and nonsmokers. | 2006-09 |
|
| Genotoxicity of glycidamide in comparison to (+/-)-anti-benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide and alpha-acetoxy-N-nitroso-diethanolamine in human blood and in mammalian V79-cells. | 2006-04 |
|
| Toxicokinetics of acrylamide in humans after ingestion of a defined dose in a test meal to improve risk assessment for acrylamide carcinogenicity. | 2006-02 |
|
| Reagent controlled addition of chiral sulfur ylides to chiral aldehydes. | 2005-08-26 |
|
| [Recent trends in evaluating risk associated with acrylamide in foods. --Focus on a new approach (MOE) to risk assessment by JECFA--]. | 2005 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 22:24:30 GMT 2025
by
admin
on
Mon Mar 31 22:24:30 GMT 2025
|
| Record UNII |
6G5ELX5XYN
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Preferred Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
Glycidamide
Created by
admin on Mon Mar 31 22:24:30 GMT 2025 , Edited by admin on Mon Mar 31 22:24:30 GMT 2025
|
PRIMARY | |||
|
5694-00-8
Created by
admin on Mon Mar 31 22:24:30 GMT 2025 , Edited by admin on Mon Mar 31 22:24:30 GMT 2025
|
PRIMARY | |||
|
DTXSID2031374
Created by
admin on Mon Mar 31 22:24:30 GMT 2025 , Edited by admin on Mon Mar 31 22:24:30 GMT 2025
|
PRIMARY | |||
|
227-163-2
Created by
admin on Mon Mar 31 22:24:30 GMT 2025 , Edited by admin on Mon Mar 31 22:24:30 GMT 2025
|
PRIMARY | |||
|
91550
Created by
admin on Mon Mar 31 22:24:30 GMT 2025 , Edited by admin on Mon Mar 31 22:24:30 GMT 2025
|
PRIMARY | |||
|
6G5ELX5XYN
Created by
admin on Mon Mar 31 22:24:30 GMT 2025 , Edited by admin on Mon Mar 31 22:24:30 GMT 2025
|
PRIMARY | |||
|
7804
Created by
admin on Mon Mar 31 22:24:30 GMT 2025 , Edited by admin on Mon Mar 31 22:24:30 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
PARENT -> METABOLITE |
|
